Mae West

The bawdy blonde actress was known as much for her busty sex appeal as her ribald one-liners (“I’ve been on more laps than a napkin!”). Undeterred after her first Broadway play, Sex (1926), landed her in jail on obscenity charges, she went on to become one of the major theater and film stars of the first half of the 20th century. West was also an early supporter of civil rights. When management prohibited her African-American lover from entering her apartment, she simply bought the whole building.

Tallulah Bankhead

Although a talented stage actress, Bankhead is perhaps best remembered for her flamboyant personality and libertine lifestyle. Always the life of the party, she was a member of the famed Algonquin Round Table and a popular Hollywood hostess. Outspoken about her lax approach to both drugs and sex, she could always be counted on for a titillating sound bite (“Cocaine isn't habit forming. I should know—I've been using it for years.”)

Marilyn Monroe

Onscreen, Monroe may have played the naïve bombshell, but off screen, she was wise to the currency of her curves. To wit, she posed nude in Playboy as the first Playmate of the Month and —rumor has it—went commando during the famous subway grate scene in The Seven Year Itch. Then, there was President Kennedy’s 45th birthday gala, where Monroe’s breathy performance of “Happy Birthday, Mr. President” turned a wholesome children’s song into an oversexed siren call to Kennedy (with whom she was reportedly having an affair). Well played, Marilyn.

Helen Gurley Brown

As the author of the groundbreaking 1962 advice book, Sex and the Single Girl, Gurley Brown paved the way for an army of Carrie Bradshaws, encouraging women to be financially independent and engage in, nay, enjoy sex before marriage. She subsequently took the helm of Cosmopolitan as the Editor-in-Chief and spent the next 32 years spreading the gospel of fab fashion and better orgasms.

Candy Darling

Born James Lawrence Slattery, Darling’s transformation into a glamorous Old Hollywood-style blonde caught the attention of Andy Warhol, who added her to his constellation of Superstars. Openly transsexual during an era when homosexuality was considered taboo, Darling was a pioneer whose life was tragically cut short at 29 by leukemia. Yet even during her final days, she never lost her wicked sense of humor. “I am just so bored by everything,” she wrote in a goodbye letter to friends. “You might say bored to death.”

Janis Joplin

Before Joplin, rock ‘n’roll was primarily a boy’s club where women were either installed as the pretty face of the band (see: Michelle Phillips) or relegated to backup singer. Joplin could go toe to toe with any of her male peers, thanks to her powerful yet husky pipes and unladylike stage presence (she was prone to swearing and swilling from a bottle of Jim Beam).

Poly Styrene

At 16, Styrene (a.k.a. Marianne Joan Elliot-Said) saw the Sex Pistols perform and thought she could do better. So she formed a band, X-Ray Spex, and, with her garish outfits and mouthful of braces, became one of punk rock’s more outrageous personas. Styrene later joined the Hare Krishnas but not before she stuck it to the man with rebellious anthems like “Oh Bondage Up Yours!”

Madonna

And so we arrive at the agent provocateur par excellence, Her Madgesty. From her pornographic coffee table tome to her lip-lock with Britney Spears, Madonna has spent the better part of her career courting controversy and making bad girl behavior marketable. She set the pace for virtually every pop princess that came after her, a fact which —no surprises here— she's always happy to mention.

Courtney Love

How could we not include the woman who said of former flame, Trent Reznor, “Don’t call your band Nine Inch Nails if you have a three-inch one”? Brash, loud, and always inappropriate, Love emerged in the spotlight as the lead singer of grunge band, Hole, and has somehow managed to remain there ever since. Never one to shy away from a juicy celebrity feud, she most recently went on record to say that Miley Cyrus had “a cr*p stylist." Meow.

Angelina Jolie

In her 20s, Jolie was a wild child to say the least. In interviews, she spoke openly about her fondness for knife-play, drugs, and bisexuality. And then there was that lingering kiss with her brother at the 2000 Oscars that raised as many eyebrows as questions. Former husband Billy Bob Thornton didn’t prove to be a good influence either; the couple reportedly wore vials of each other’s blood. Of course, all that is behind Jolie now that she has Brad and their brood. So if you happen to cross paths, it’s probably not wise to bring it up.

M.I.A.

Rapper Mathangi "Maya" Arulpragasam (a.k.a. M.I.A.) is a lighting rod for controversy. Her politics, specifically her support of Sri Lankan militant group, Tamil, landed her on the U.S. Homeland Security risk list in 2006 while her 2010 “Born Free” video was pulled from YouTube due to its footage of U.S. soldiers beating people with their guns. She’s also no friend to the mainstream media and famously tweeted The New York Times journalist Lynn Hirschberg’s phone number after she penned an unfavorable profile. Oof. That's harsh.

Rihanna

A classic case of a good girl gone bad, Rihanna evolved from a cheerful pop star who would let you stand under her "umbrella" to a black leather-clad vamp who claimed that “whips and chains” excited her. These days, she chronicles her naughty exploits on her Instagram account, which is filled with images of the singer puffing marijuana and posing provocatively like this, and this, and oh, also this.